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Synlett 2016; 27(07): 1027-1040
DOI: 10.1055/s-0035-1561954
DOI: 10.1055/s-0035-1561954
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Phosphoric Acid Based Heterodimers in Asymmetric Catalysis
Further Information
Publication History
Received: 25 February 2016
Accepted: 09 March 2016
Publication Date:
29 March 2016 (online)
‡ These two authors contributed equally.
Abstract
Chiral phosphoric acid diesters arguably constitute the most exploited class of catalysts in asymmetric Brønsted acid catalysis. Despite being highly investigated for their acidic properties, these compounds display an amphoteric nature, which has instead been considerably overlooked. The potential of this dichotomous polarity has recently been disclosed and applied to the development of novel reaction modes in organocatalysis. In this account, we present our recent advances in this area, focusing on the establishment of heterodimeric interactions toward the nucleophilic activation of carboxylic acids, thiocarboxylic acids and ketones (via their enols) in asymmetric transformations.
1 Introduction
2 Discovery of Heterodimeric Self-Assemblies
3 Activation of Carboxylic Acids
3.1 The Enantioselective Carboxylysis of Aziridines
3.2 An Asymmetric Hydrolysis of Epoxides
4 Activation of Thiocarboxylic Acids
5 Enol Catalysis
5.1 Asymmetric Michael Addition
5.2 Asymmetric α-Amination
5.3 Asymmetric α-Allylation
6 Concluding Remarks
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For recent developments on phosphoric acid catalysis, see Synlett cluster 2016, Asymmetric Phosphoric Acid Catalysis:
For similar observations on a different phosphoric acid catalyst, see:
For the instability of phosphoric acids toward epoxides see:
For metal-based asymmetric thiolysis reactions, see:
For related organocatalytic reactions, see:
For selected studies on acid-catalyzed enolizations of ketones, see:
For a review, see:
For recent reviews/accounts on asymmetric enamine catalysis, see:
For recent reviews on the asymmetric synthesis of quaternary stereocenters, see:
For selected examples, see:
For a recent highlight on Tsuji–Trost allylic alkylations with ketone enolates, see:
For selected reports, see: